Karen:
First date: Actually, her fake dates with Haruhi were the only ones she's ever been on.
First kiss: Karen has decided that kisses don't count if they happen under significant emotional stress or are community-imposed, and she therefore hasn't had her first kiss. For those of you who are not in denial, ::moves Clue piece:: it was Kaito, in the greenhouse, with the magic trick.
First crush: Nozomi, not that she really realized that was what it was until later.
First time: FIND A VIRUS TO BE A WHORE.

Cinnamon has had none of these.

Radd:
First date: This is kind of hard to pin down. He did all kinds of stuff that might be considered dating depending on how loosely you define it, but it's also perfectly possible that he's never actually been on one.
First kiss: With Sheena, shortly after reviving Bogey.
First crush: Actually, Radd kind of skipped the whole "crush" phase entirely, having come preprogrammed with a girlfriend. Their relationship wasn't always a sure thing, mind you, but...
First time: Uh, Kid Radd isn't that type of game.